Sodium hydride → tert-butyl 3-{N-formyl-N-[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino)propylcarbamate

HRID 1247809Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1247809
[CH3:1][N:2]1[C:6]([NH:7][C:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:5]([NH:27][CH:28]=[O:29])[CH:4]=[N:3]1.[H-].[Na+].Br[CH2:33][CH2:34][CH2:35][NH:36][C:37](=[O:43])[O:38][C:39]([CH3:42])([CH3:41])[CH3:40].S([O-])(O)(=O)=O.[K+]>CN(C)C=O.[I-].[Na+]>[CH:28]([N:27]([CH2:33][CH2:34][CH2:35][NH:36][C:37](=[O:43])[O:38][C:39]([CH3:42])([CH3:41])[CH3:40])[C:5]1[CH:4]=[N:3][N:2]([CH3:1])[C:6]=1[NH:7][C:8]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:29]

Komponenten

7

Edukt 4

HCID 24758Sodium hydrideHCID 516920Potassium bisulfateHCID 4460490tert-butyl N-(3-bromopropyl)carbamateHCID 21904512[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]formamide

Produkt 1

HCID 21904462tert-butyl 3-{N-formyl-N-[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino)propylcarbamateAusbeute 50,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 5238Sodium IodideLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a solution of N-[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]formamide (3.825 g) in N,N-dimethylformamide (66 ml) was added sodium hydride (264 mg, 60% oil suspension) under a nitrogen atmosphere at 0° C. under stirring. The mixture was stirred at 0° C. for 15 minutes. To the mixture were added tert-butyl N-(3-bromopropyl)carbamate (2.62 g) in N,N-dimethylformamide (10 ml) and sodium iodide (1.65 g). The mixture was warmed to room temperature and stirred for 2 hours. 10% Aqueous potassium hydrogen sulfate solution (5 ml) was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was chromatographed on silica gel eluting with methylene chloride/ethyl acetate (4:1) to give tert-butyl 3-{N-formyl-N-[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}propylcarbamate (2.714 g). The NMR spectrum of this compound indicates the existence of its rotamer.

Aufarbeitung

  1. stirringThe mixture was stirred at 0° C. for 15 minutes
  2. stirringstirred for 2 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was chromatographed on silica gel eluting with methylene chloride/ethyl acetate (4:1)

Quellen und Nachweise

ORD-Eintrag
ord-03a25df27de24cbf96d444c0de47a7d2
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07129232B2

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